[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

EP0267670B1 - Composés optiquement actifs, qui sont des cristaux liquides, contenant un groupe de cyano - Google Patents

Composés optiquement actifs, qui sont des cristaux liquides, contenant un groupe de cyano Download PDF

Info

Publication number
EP0267670B1
EP0267670B1 EP87307217A EP87307217A EP0267670B1 EP 0267670 B1 EP0267670 B1 EP 0267670B1 EP 87307217 A EP87307217 A EP 87307217A EP 87307217 A EP87307217 A EP 87307217A EP 0267670 B1 EP0267670 B1 EP 0267670B1
Authority
EP
European Patent Office
Prior art keywords
liquid crystal
compound
optically active
formula
active liquid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP87307217A
Other languages
German (de)
English (en)
Other versions
EP0267670A1 (fr
Inventor
Kazutoshi Miyazawa
Takashi Inukai
Hiromichi Inoue
Shinichi Saito
Kouji Ohno
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
Chisso Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chisso Corp filed Critical Chisso Corp
Publication of EP0267670A1 publication Critical patent/EP0267670A1/fr
Application granted granted Critical
Publication of EP0267670B1 publication Critical patent/EP0267670B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2021—Compounds containing at least one asymmetric carbon atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458—Uncondensed pyrimidines
    • C09K19/3463—Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines

Definitions

  • This invention relates to a novel liquid crystalline compound and a liquid crystal composition containing the same. More particularly it relates to a liquid crystalline compound having an optically active group and a chiral liquid crystal composition containing the same.
  • the liquid crystalline compound defined in the present application includes not only compounds which are possible to observe their crystalline state by themselves, but also compounds which are impossible to observe their crystalline state, but nevertheless have a chemical structure similar to those of liquid crystal compounds and also have properties useful as a constituent of liquid crystal compositions.
  • TN (Twisted Nematic) mode display has been most broadly employed for liquid crystal elements, but this mode is inferior in the aspect of response rate to emissive mode display elements such as electroluminescent display, plasma display, etc.
  • emissive mode display elements such as electroluminescent display, plasma display, etc.
  • various attempts in this respect have been made, but nevertheless a possibility of improvement to a large extent does not seem to remain so much.
  • various attempts for obtaining a liquid crystal display device based on another principle, in place of TN mode display elements have been made.
  • there is a display mode making use of ferroelectric liquid crystals N.A. Clark et al: Applied Phys. lett., 36 899 (1980)).
  • This mode makes use of ferroelectric liquid crystal chiral smectic C phase (hereinafter abbreviated to SC* phase) or chiral smectic H phase (hereinafter abbreviated to SH*), and has the following three superior specific feature as compared with TN mode display:
  • the first specific feature is that the display elements have a very high response rate which amounts to 100 times those of TN mode display elements.
  • the second specific feature is that the elements have a memory effect so that the multiplex drive is easy in combination with the above high rate response properties.
  • the third specific feature is that only by adjusting the reverse time of polarity, it is possible to easily obtain the gray scale as compared with TN type display mode, and hence the display mode has been considered to be suitable for graphic display.
  • the present inventors have searched for various liquid crystal compounds having an optically active group mainly in order to develop liquid crystal compounds having specific features, particularly those having a large spontaneous polarization value, suitable for being utilized for the above display mode, and as a result have achieved the present invention.
  • the present invention resides in an optically active liquid crystalline compound expressed by the formula: wherein m represents an integer of 2 to 6 l represents an integer of 0 to 7; n represents 0 or 1; R represents an alkyl group or an alkoxy group each of 2 to 12 carbon atoms, or a cyano group; and A and B each represent a group of formula: (wherein X represents a hydrogen atom, a fluorine atom, a chlorine atom or cyano group) or A may represent a single bond; and a chiral smectic liquid crystal composition containing at least one kind of the above compound.
  • phase transition points and the spontaneous polarization values Ps of representative compounds of the formula (I) are shown in Tables 1 and 2.
  • liquid crystal compositions using the compounds of the formula (I)
  • it is also possible to prepare chiral smectic liquid crystal compositions by mixing the compounds of the formula (I) with other smectic liquid crystal compositions.
  • the compound of the formula (I) is added in a suitable quantity to a smectic C liquid crystal composition, it is possible to prepare a liquid crystal compound exhibiting chiral smectic C phase.
  • examples of materials for smectic C liquid crystal compositions are 5-alkyl-2-(4'-alkoxyphenyl)-pyrimidine compounds represented by 5-octyl-2-(4'-octyloxyphenyl)-pyrimidine, 5-octyl-2-(4'-nonyloxyphenyl)-pyrimidine, 5-octyl-2-(4'-decyloxyphenyl)-pyrimidine, etc., 5-alkyl-2-(4'-alkoxyphenyl)-pyridine compounds represented by 5-heptyl-2-(4'-octyloxyphenyl)-pyridine, 5-octyl-2-(4'-octyloxyphenyl)-pyridine, 5-heptyl-2-(4'-nonyloxyphenyl)-pyridine, 5-nonyl-2-(4'-nonyloxyphenyl)-pyridine, etc., 4-alkoxyphen
  • the compound of the formula (I) has an optically active carbon; hence when the compound is added to nematic liquid crystals, it has a capability of inducing a twisted structure. Since the nematic liquid crystals i.e. chiral nematic liquid crystals do not form the so-called reverse domain (reverse domain dechiralization lines) of TN mode display elements, the compound of the formula (I) is usable as an agent for preventing the reverse domain.
  • the compound of the formula (I) is suitably prepared by the following passageways: wherein, l, m, n, *, R, A and B are as defined above, respectively and Ts represents a p-toluenesulfonyl group
  • o-bromophenol or 3-bromo-4-hydroxybiphenyl (II) each as a known substance is subjected to methyl etherification into a compound (III), which is then reacted with an acid halide such as acetyl chloride to obtain a compound (IV), which is further reacted with hydrobromic acid for demethylation to obtain a compound (V).
  • This compound (V) may also be prepared by directly acetylizing the compound (II) according to a process as described in Example 3.
  • the compound (V) is reacted with an alkyl tosilate as shown by a compound (X) to obtain a compound (VI), which is then reacted with a cyanogenating agent such as cuprous cyanide to obtain a compound (VII).
  • a cyanogenating agent such as cuprous cyanide
  • This compound (VII) is oxidized into a compound (VIII), which is reacted with a halogenating agent such as thionyl chloride to obtain an acid halide (IX).
  • the compound (IX) is reacted with a phenol (XI) such as p-alkylphenols, p-alkoxyphenols, 4 ⁇ -alkyl-4-phenylphenols, 4 ⁇ -alkoxy-4-phenylphenols, etc. to obtain the objective compound (I).
  • preparation of the compound (VIII) is substantially important, since preparation passageways from the compound (VIII) into the compound (I) are a mere esterification reaction.
  • the compound (VIII) may be also prepared from the compound (VI) through the following passageways:
  • optically active liquid crystalline compound of the present invention will be described in more detail by way of Examples.
  • aqueous sodium hypobromate solution prepared from NaOH (102 g), Br2 (117 g) and water (500 ml) was added over 30 minutes to the above ketone (82 g) dissolved in p-dioxane (100 ml) at 15° ⁇ 20°C, followed by keeping the mixture at 50°C for 2 hours, treating with sodium bisulfite to destroy excess of the oxidant.
  • the carboxylic acid precipitated by acidification with 6N hydrochloric acid was recrystallized from acetic acid to obtain S 3 ⁇ bromo-4 ⁇ -(6-methyloctyloxy)-4-biphenylcarboxylic acid (46 g) (C-S, 97.5°C, S-I, 137.3°C).
  • optically active 3 ⁇ -cyano-4 ⁇ -(alkoxy)-4-biphenylcarboxylic acids were prepared in a similar way.
  • a liquid crystal composition 1 consisting of the following compone nts and having a SC* phase having a spontaneous polarization value of 1 nC/cm2 or less was prepared:
  • phase transition points of this composition are as follows:
  • This composition was filled in a cell of 2 ⁇ m thick provided with transparent electrodes each obtained by applying PVA as an aligning agent thereonto and rubber the resulting surface to subject it to parallel aligning treatment, followed by placing the resulting cell between two sheets of crossed polarizers and impressing a square wave having a wave height of 10 V.
  • change in the intensity of transmitted light was observed. Its response time was sought from the change in the intensity of transmitted light at that time to give a value of about 3 ⁇ sec at 25°C.
  • the resulting liquid crystal composition 2 had the following phase transition points: And its spontaneous polarization value at 25°C was 9.9 nC/m2 and its tilt angle was 20.5°.
  • the response time of this composition was sought in the same manner as in the case of the composition 1 to give 220 ⁇ sec.
  • Example 5 (Use example 2)
  • Example 4 To the liquid crystal composition 1 of Example 4 was added a compound of Example 2 of the present invention (compound No. 30) in 20% by weight.
  • the resulting liquid crystal composition 3 had the following phase transition points: Its spontaneous polarization value at 25°C was 10.6 nC/cm2 and its tilt angle was 20°.
  • This composition 3 was filled in a cell of 2 ⁇ m thick provided with transparent electrodes each obtained by applying PVA as an aligning agent thereonto and rubbing the resulting surface to subject it to parallel aligning treatment, followed by placing the resulting cell between two sheets of crossed polarizers and impressing a square wave having a wave height of 10 V.
  • PVA an aligning agent
  • rubbing the resulting surface to subject it to parallel aligning treatment
  • impressing a square wave having a wave height of 10 V As a result, change in the intensity of transmitted light was observed. Its response time was sought from the change in the intensity of transmitted light at that time to give a value of 210 ⁇ sec at 25°C.
  • Example 6 (Use example 3)
  • a composition consisting of the following components and being an achiral substance and having SC phase:
  • Example 1 of the present invention compound No. 7
  • compound No. 7 a compound of Example 1 of the present invention
  • the spontaneous polarization value at 25°C of this composition was 8.0 nC/cm2 and its tilt angle was 20°.
  • This composition was filled in a cell of 2 ⁇ m thick provided with transparent electrodes each obtained by applying PVA as an aligning agent thereonto and rubbing the resulting surface to subject it to parallel aligning treatment, followed by placing the resulting cell between two sheets of crossed polarizers and impressing a square wave having a wave height of 10 V.
  • PVA an aligning agent
  • rubbing the resulting surface to subject it to parallel aligning treatment
  • impressing a square wave having a wave height of 10 V As a result, change in the intensity of transmitted light was observed. Its response time was sought from the change in the intensity of transmitted light at that time to give a value of 270 ⁇ sec.
  • Example 3 To the liquid crystal composition 1 of Example 3 was added the following compound of a structure having CN group of the compound of the present invention replaced by F atom in 20% by weight: to obtain a liquid crystal composition. Its phase transition points were as follows: This composition had a spontaneous polarization value at 25°C of 1.7 nC/cm2 and a tilt angle of 26°.
  • addition of the compound of the present invention having cyano group at a position very close to the asymmetrical carbon exhibits a notable effectiveness in the aspect of the response time as compared with addition of other similar compounds.
  • Example 7 (Use example 4)
  • a nematic liquid crystal composition consisting of was filled in a cell provided with transparent electrodes each obtained by applying polyvinyl alcohol (PVA) thereonto and rubbing the resulting surface to subject it to a parallel aligning treatment and having a distance between the electrodes of 10 ⁇ m to prepare a TN mode cell.
  • PVA polyvinyl alcohol
  • This cell was observed under a polarizing microscope.
  • formation of a reverse twist domain was observed.
  • a compound of Example 2 of the present invention was added in 0.1% by weight to this TN mode cell, it was observed that the reverse twist domain dissolved and a uniform nematic phase was observed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (9)

  1. Un composé cristallin liquide optiquement actif représenté par la formule:
    Figure imgb0042
     dans laquelle m représente un nombre entier de 2 à 6; l représente un nombre entier de 0 à 7; n représente 0 ou 1; R représente un groupement alkyle ou un groupement alcoxy de 2 à 12 atomes de carbone, un groupement nitrile et A et B représentent chacun un groupement de la formule:
    Figure imgb0043
     (dans laquelle X représente un atome d'hydrogène, un atome de fluor, un atome de chlore ou un groupement nitrile) ou A peut représenter une liaison simple.
  2. Un composé cristallin liquide optiquement actif suivant la Revendication 1, dans lequel l dans la formule (I) est zéro.
  3. Un composé cristallin liquide optiquement actif suivant la Revendication 1, dans lequel l dans la formule (I) est 1 à 7.
  4. Un composé cristallin liquide optiquement actif suivant l'une quelconque des Revendications précédentes, dans lequel R représente un groupement alkyle ou un groupement alcoxy de 4 à 12 atomes de carbone.
  5. Un composé cristallin liquide optiquement actif suivant l'une quelconque des Revendications précédentes, dans lequel R représente un groupement alkyle ou un groupement alcoxy de 6 à 8 atomes de carbone.
  6. Un composé cristallin liquide optiquement actif suivant l'une quelconque des Revendications précédentes, dans lequel A représente une liaison simple ou un groupement de formule:
    Figure imgb0044
  7. Un composé cristallin liquide optiquement actif suivant l'une quelconque des Revendication précédentes, dans lequel B représente un groupement de formule:
    Figure imgb0045
  8. Une composition à base de cristaux liquides smectiques chirale comprenant au moins deux composants dont au moins un est un composé cristallin liquide tel que défini dans l'une quelconque des Revendications précédentes.
  9. Un élément de commutation de la lumière basé sur une composition cristalline liquide telle que décrite dans la Revendication 8.
EP87307217A 1986-08-18 1987-08-14 Composés optiquement actifs, qui sont des cristaux liquides, contenant un groupe de cyano Expired EP0267670B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP61192516A JP2554473B2 (ja) 1986-08-18 1986-08-18 シアノ基を有する新規光学活性液晶化合物
JP192516/86 1986-08-18

Publications (2)

Publication Number Publication Date
EP0267670A1 EP0267670A1 (fr) 1988-05-18
EP0267670B1 true EP0267670B1 (fr) 1992-12-23

Family

ID=16292584

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87307217A Expired EP0267670B1 (fr) 1986-08-18 1987-08-14 Composés optiquement actifs, qui sont des cristaux liquides, contenant un groupe de cyano

Country Status (4)

Country Link
US (1) US4886622A (fr)
EP (1) EP0267670B1 (fr)
JP (1) JP2554473B2 (fr)
DE (1) DE3783213T2 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4780240A (en) * 1985-08-02 1988-10-25 Chisso Corporation Liquid crystal composition
DE3600052A1 (de) * 1986-01-03 1987-07-09 Merck Patent Gmbh Heterocyclische verbindungen
JPH0832673B2 (ja) * 1987-03-20 1996-03-29 チッソ株式会社 オルト−シアノ−ベンゼン骨格を含む光学活性液晶化合物
JPH0768518B2 (ja) * 1987-07-08 1995-07-26 チッソ株式会社 強誘電性液晶組成物
US4959173A (en) * 1987-09-29 1990-09-25 Adeka Argus Chemical Co., Ltd. Optically active ester compound
US5238603A (en) * 1987-10-15 1993-08-24 Chisso Corporation Optically active liquid crystalline compound and a composition containing same
JP2534283B2 (ja) * 1987-11-26 1996-09-11 チッソ株式会社 強誘電性液晶組成物
JPH01256590A (ja) * 1988-04-06 1989-10-13 Chisso Corp 強誘電性液晶組成物および液晶素子
US5145601A (en) * 1990-06-25 1992-09-08 The University Of Colorado Foundation Inc. Ferroelectric liquid crystals with nicotinic acid cores
US5128061A (en) * 1990-08-14 1992-07-07 Optical Shields, Inc. Phenyl-pyrimidine liquid crystal materials
US5344585A (en) * 1990-09-14 1994-09-06 Hoechst Aktiengesellschaft Use of 4-fluoropyrimidine derivatives as component for ferroelectric liquid crystal mixtures
EP0513262B1 (fr) * 1990-11-27 2000-04-05 MERCK PATENT GmbH 2-fluoropyridines 3,6-disubstituees
DE19500760A1 (de) * 1995-01-13 1996-07-18 Basf Ag Substituierte 2-Phenylpyridine
US6413448B1 (en) 1999-04-26 2002-07-02 Displaytech, Inc. Cyclohexyl- and cyclohexenyl-substituted liquid crystals with low birefringence
US7195719B1 (en) 2001-01-03 2007-03-27 Displaytech, Inc. High polarization ferroelectric liquid crystal compositions
US6838128B1 (en) 2002-02-05 2005-01-04 Displaytech, Inc. High polarization dopants for ferroelectric liquid crystal compositions

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2309509A1 (fr) * 1975-04-30 1976-11-26 Thomson Csf Nouveau compose organique, melange mesomorphe a grande diffusion dynamique comportant ledit compose, et procede de fabrication dudit compose
GB1596012A (en) * 1976-08-16 1981-08-19 Secr Defence Optically active liquid crystal materials and liquid crystal devices containing them
US4225736A (en) * 1979-04-17 1980-09-30 Sun Oil Company Of Pennsylvania Codimer of norbornadiene and cyclohexadiene
GB2053193B (en) * 1979-05-01 1983-05-05 Suwa Seikosha Kk 2'-cyano-4'-n-alkylphenyl 3-cyano-4-n-alkoxybenzoates
DE3014912A1 (de) * 1979-05-15 1980-11-27 Werk Fernsehelektronik Veb Nematische fluessigkristalline 5-cyan- 2- eckige klammer auf 4-acyloxyphenyl eckige klammer zu -pyrimidine und diese enthaltende gemische
FR2461697A1 (fr) * 1979-07-20 1981-02-06 Suwa Seikosha Kk 3-cyano-4-alcoxybenzoate de 2-chloro-4-alcoylphenyle et son utilisation dans une composition de cristaux liquides
EP0025119B1 (fr) * 1979-08-20 1983-05-25 VEB Werk Für Fernsehelektronik im VEB Kombinat Mikroelektronik Cristaux liquides nématiques de 5-alkyl-2-(4-acyloxyphényl)-pyrimidines destinés à des dispositifs opto-électroniques et procédé pour leur préparation
JPS6028487A (ja) * 1983-07-27 1985-02-13 Alps Electric Co Ltd 液晶組成物
JPH0794406B2 (ja) * 1984-02-08 1995-10-11 チッソ株式会社 液晶性置換ビフエニルエステル類
FR2561657B1 (fr) * 1984-03-20 1988-02-19 Thomson Csf Procede d'obtention d'un cristal liquide smectique c chiral ferroelectrique cristal liquide obtenu par ce procede et dispositif de visualisation utilisant ce cristal liquide
GB8415039D0 (en) * 1984-06-13 1984-07-18 Secr Defence Pyrimidines
FR2567877B1 (fr) * 1984-07-17 1986-11-14 Thomson Csf Compose organique a structure chirale, son utilisation dans un melange de cristaux liquides et son procede de fabrication
JPS61122250A (ja) * 1984-11-20 1986-06-10 Citizen Watch Co Ltd 液晶性エステル化合物
JPH0610170B2 (ja) * 1984-12-26 1994-02-09 チッソ株式会社 新規光学活性化合物及び液晶組成物
DE3685032D1 (de) * 1985-01-09 1992-06-04 Dainippon Ink & Chemicals Substituierte fluessigkristallverbindungen.
EP0191600B1 (fr) * 1985-02-08 1991-12-27 Ajinomoto Co., Inc. Composés esters à base de polyphényles et compositions de polyphényles les contenant
JPS61210056A (ja) * 1985-03-14 1986-09-18 Chisso Corp 含ハロゲン光学活性液晶化合物及び液晶組成物
DE3515373A1 (de) * 1985-04-27 1986-11-06 Merck Patent Gmbh, 6100 Darmstadt Stickstoffhaltige heterocyclen
DE3518734A1 (de) * 1985-05-24 1986-11-27 Merck Patent Gmbh, 6100 Darmstadt Smektische fluessigkristalline phasen
US4780240A (en) * 1985-08-02 1988-10-25 Chisso Corporation Liquid crystal composition
EP0233267B1 (fr) * 1985-09-18 1994-08-03 MERCK PATENT GmbH Phases smectiques a cristaux liquides
DE3604462A1 (de) * 1986-02-13 1987-08-20 Merck Patent Gmbh Smektische fluessigkristalline phasen
DE3706766A1 (de) * 1986-03-14 1987-09-17 Merck Patent Gmbh Smektische fluessigkristalline phasen
JPH0735352B2 (ja) * 1986-04-25 1995-04-19 チッソ株式会社 ３−置換ビフエニル化合物
JPS63130574A (ja) * 1986-11-18 1988-06-02 Asahi Glass Co Ltd ビフエニルカルボン酸フエニルエステル誘導体およびそれを用いた強誘電性スメクチツク液晶組成物
JPH0678972A (ja) * 1992-09-07 1994-03-22 Sekisui Chem Co Ltd 蒸気滅菌器及びその制御方法
JPH06222889A (ja) * 1993-01-25 1994-08-12 Canon Inc 周辺装置コントローラ

Also Published As

Publication number Publication date
JP2554473B2 (ja) 1996-11-13
US4886622A (en) 1989-12-12
DE3783213T2 (de) 1993-04-29
EP0267670A1 (fr) 1988-05-18
DE3783213D1 (de) 1993-02-04
JPS6348254A (ja) 1988-02-29

Similar Documents

Publication Publication Date Title
EP0267670B1 (fr) Composés optiquement actifs, qui sont des cristaux liquides, contenant un groupe de cyano
US4737313A (en) Liquid-crystalline substituted biphenyl esters
EP0152217B1 (fr) Cristaux liquides d'esters d'acide carbonique et compositions de cristaux liquides les contenant
EP0197677A2 (fr) Composé liquide cristallin optiquement actif contenant des halogènes et composition liquide cristalline le contenant
EP0243209B1 (fr) Composé de biphénile 3-substitué
JPH0533943B2 (fr)
EP0244939A1 (fr) Composé de pyridine contenant d'halogène et composition cristalline liquide
US4623477A (en) Ester compounds having a pyrimidine ring
EP0306195B1 (fr) Diphényl-2,5 pyridines optiquement actives
JPH0688952B2 (ja) メチレンオキシ基とエステル基を有する新規光学活性液晶化合物及びその組成物
US4913838A (en) Liquid crystal compound with a 4-(optically active alkyl)-3-cyanophenyl group
EP0225728B1 (fr) Ester d'acide carbonique cristal liquide et composition liquide cristalliné le contenant
EP0272115B1 (fr) Composés biphényliques cristallins liquides optiquement actifs
EP0260910A1 (fr) Diphényl-3,6 pyridazines
JPS63122651A (ja) フルオロアルカン誘導体、それを含む液晶組成物および液晶素子
US4895671A (en) Optically active phenylpyrimidine compound and a liquid crystal composition
Decobert et al. Synthesis and mesomorphysm of some new ferro-electric smectic liquid crystals
EP0313338B1 (fr) Biphényl-2-pyridines optiquement actives
EP0329153B1 (fr) Dérivé d'acide lactique et composition liquide cristalline le contenant
JPS63104949A (ja) フルオロアルカン誘導体及びこれを含む液晶組成物及び液晶素子
EP0312210B1 (fr) Composés liquides cristallins optiquement actifs et compositions les contenant
JPH0578548B2 (fr)
JPH01121244A (ja) 光学活性な液晶性化合物、それを含有する液晶組成物およびそれを使用した液晶素子
EP0256307B1 (fr) Composés optiquement actifs ayant une structure biphénylique, composition à base de cristaux liquides et commutateur optique les contenant
US5665270A (en) Optically active trifluorolactic acid derivative and liquid crystal composition

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): CH DE FR GB LI

17P Request for examination filed

Effective date: 19880701

17Q First examination report despatched

Effective date: 19891030

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): CH DE FR GB LI

REF Corresponds to:

Ref document number: 3783213

Country of ref document: DE

Date of ref document: 19930204

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19960809

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19960821

Year of fee payment: 10

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19960823

Year of fee payment: 10

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19970831

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19970831

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980430

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19980501

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20010808

Year of fee payment: 15

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20020814

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20020814